Will & Harper (& You)
Reflections on friendship & empathy thanks to Will Ferrell and Harper Steele's new documentary
This Friday the rain came, and I watched from the inside as the world softened around me. The gray clouds cast a blue haze on the rest of us below. The pitter patter of raindrops on the window acted as an invitation to quiet my thoughts and give in to warmth of my bed. Stay in, stay in, they tapped on the glass, and I happily obliged.
This was especially welcome, as the second half of September was a bit of a whirlwind. I met a high school friend in Barcelona for a few days before she flew into Munich the same day my cousin did. Putting on the hostess hat for 10-days straight demands a good amount of energy and planning, but it’s also a hat I’m grateful to wear. We visited museums and lakes and beer gardens, ate far too much meat (lol), and attended our first ever Oktoberfest! Good times were had by all.






Still, a true introvert at heart, I needed a day to activate my Sloth Mode in order to recharge my social battery and continue on. So, on this rainy Friday, my cousin ventured out into the city on his own (they grow up so fast🥲) and I retreated to my bed with my laptop.
That’s when I remembered that Will & Harper came out that day. I had seen the trailer a few weeks ago, and after watching this interview with Seth Meyers, I decided now was as perfect a time as ever to check it out:
There is SO MUCH I WANT TO SAY. But perhaps the most important thing I should say is: go and watch it yourself. (Then maybe pop into my DMs or email or texts, and we can discuss together!)
In case you didn’t watch the video above, here’s the documentary blurb:
When Will Ferrell finds out his close friend of 30 years is coming out as a trans woman, the two decide to embark on a cross-country road trip to process this new stage of their relationship in an intimate portrait of friendship and transition.
Many things stick out about this film. It’s a crash course on empathy, and it’s a non-intimidating way for people to learn more about the transgender experience. (Especially as 1.3 million people identify as transgender in the USA, there is real value in getting to know and understand each other.)
Unfortunately, being transgender has gotten wrapped up into the dark side of politics, where now the simple existence of a trans person can cause polarizing reactions. Harper says it herself in the documentary: “Look, I'm not a very political person, but just by nature of being trans, I'm now a political person in a way.”1
I believe it’s far easier to make people fear and hate something they don’t know or understand, which is why I commend Will Ferrell and Harper Steele for creating this documentary. Allowing Will to ask any question to Harper — no matter how taboo or personal it is — and giving space for these dialogues and revelations to exist is remarkable for the audience, and for these two friends. Questions about her changing body, about hope for future love, about Harper’s new relationship to beauty, about her childhood, about why she chose the name Harper.2
At one point Will prefaces a question by saying “This is a big one, maybe we save this for later…” and Harper graciously responds, “You are a friend of mine. I invite any friend of mine to ask me these questions. I am not afraid to talk about it.”
Can you imagine the world we could live in if this was our reaction to one another? Genuine curiosity about what we do not understand? Embracing others’ “ignorance” as an opportunity to gently educate them?
Above all, what brought me to tears multiple times throughout this documentary was the pureness and sincerity of Will and Harper’s friendship.
This whole documentary came about because Harper used to travel the USA extensively (“I’ve been around this country almost as much as a truck driver,” she says) and loves it so much — yet she feared that the country no longer loved her back.
That’s when Will suggested they travel the country together, where they visit all the kinds of places Harper loved before her transition, but now as this new version of her. From a dive bar in Oklahoma to her childhood home in Iowa to a gimmicky steakhouse in Texas and beyond.
Pause for a second.
Just think about it.
Here are two people who met at work in 1995 and have been close friends for almost thirty years. When one friend (Harper) takes a step into the unknown, forced to be more open and vulnerable than they’ve ever been in their entire life, the other friend (Will) immediately shows up to support them.
Truly, this was demonstrated time and time again in the documentary. Sure, there were times when things didn’t go as smoothly as planned, but Will and Harper navigated those emotions together. They forgave. They found a new rhythm with one another.
It just made me so freaking happy that I live in a world where a friendship like Will and Harper’s exists.
One of the biggest takeaways is that we all have the opportunity to be the Will to the Harpers in our own lives. Ride beside them on their journey (literally or metaphorically). Ask tough questions. Receive tough answers. Mess up. Forgive. Try again. Laugh. Love. Move forward, together.
(Okay another big takeaway is that I desperately need to keep two soccer chairs and a cooler in my car at all times. You never know when you need to pull over to admire a beautiful view and drink a beer with a lifelong buddy.)

In conclusion, I suggest you check out this documentary if…
You don’t personally know a transman or transwoman and wish to learn more
You have trans family/friends and want to know how to best support them
Your only frame of reference is what politicians say about transgender people
You’re a Will Ferrell and/or Saturday Night Live fan3
You have ever felt weird or lonely or different from others (psst…you’re not alone!)
You ever wanted to go on a cross country road trip (I feel like I did it in under 2 hours!)
You have a sneaky suspicion that America isn’t as horrible or divided as it appears to be online or in the news…
You are a human being who with a desire to learn, love, and connect with other human beings
To be able to say “I’m not a political person” or think “Politics don’t have a real effect on our lives” is a real privilege. If this is the case for you, I hope you can shift your focus on supporting your friends and family members and fellow human beings who ARE affected by politics, fear-mongering, and dehumanizing labels such as “monsters, vermin, cockroaches, aliens” etc.
This documentary is about Harper’s journey specifically, and she doesn’t speak on behalf of every transgender woman or man.
So many SNL cameos! Harper Steele, before she transitioned, was an SNL writer from 1995-2008. Unsurprisingly, the SNL people seem extremely supportive. Reminds me of how theatre shows like The Laramie Project and The Vagina Monologues were fundamental to my teenage self’s understanding of the larger world. I love theatre people and how open and accepting they are <3
Lorelei and I are very much looking forward to watching this. Just watching the trailer together had us sobbing uncontrollably. And your article has me in tears, too. Thanks for this wonderful review and bringing your own personal take on human connection to the conversation. This topic is so very near dear to my heart and it makes me so happy that I have such kind and empathetic friends.
Oh my gosh, I would have forgotten about these two and the road trip! Your dad and I saw them on Seth and they were charming together. Gonna watch it tonight. Great write up.